Hydrogen bond mediated enantioselectivity of radical reactions

被引：73

作者：

Aechtner, T ^{[1
]}

Dressel, M ^{[1
]}

Bach, T ^{[1
]}

机构：

[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 43期

关键词：

asymmetric synthesis; cyclization; enantioselectivity; hydrogen bonds; radical reactions;

D O I：

10.1002/anie.200461222

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The chiral completing reagent 1 used in the reductive cyclization of 3-(ω-iodoalkylidene)piperidin-2-ones in the presence of Bu3SnH and with BEt3 as the initiator (see scheme) leads to good enantioselectivities thanks to its hydrogen bond mediated association with the radical intermediate. As this example shows, high stereoselectivities are possible for radical reactions proceeding through H-bonded intermediates.

引用

页码：5849 / 5851

页数：3

共 43 条

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[10] Stereoselective radical reactions
Bar, G
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[J]. CHEMICAL SOCIETY REVIEWS, 2003, 32 (05) : 251 - 263

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